N-(4-chlorophenyl)propanethioamide → [[2-(1,5-dihydro-3-methoxy-1-methyl-5-oxo4H-1,2,4-triazol-4-yl)phenyl]methyl]N-(4-chlorophenyl)propanimidothioate

HRID 1106694ノート

反応式

HRID 1106694 の反応式
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[C:13]([O:14][CH3:15])=[N:12][N:11]([CH3:16])[C:10]1=[O:17].[Cl:18][C:19]1[CH:29]=[CH:28][C:22]([NH:23][C:24](=[S:27])[CH2:25][CH3:26])=[CH:21][CH:20]=1.CC(C)([O-])C.[K+]>C1COCC1.C(OCC)(=O)C>[CH3:15][O:14][C:13]1[N:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[CH2:2][S:27][C:24](=[N:23][C:22]2[CH:21]=[CH:20][C:19]([Cl:18])=[CH:29][CH:28]=2)[CH2:25][CH3:26])[C:10](=[O:17])[N:11]([CH3:16])[N:12]=1

参加物

6

反応物 3

HCID 4154740N-(4-chlorophenyl)propanethioamideHCID 110338324-[2-(Bromomethyl)phenyl]-2,4-dihydro-5-methoxy-2-methyl-3H-1,2,4-triazol-3-oneHCID 23665647Potassium tert-butoxide

生成物 1

HCID 15457013[[2-(1,5-dihydro-3-methoxy-1-methyl-5-oxo4H-1,2,4-triazol-4-yl)phenyl]methyl]N-(4-chlorophenyl)propanimidothioate収率 95%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 0.50 g of the title compound of Step D in 2 mL of THF was added 0.37 g of 4'-chlorothiopropionanilide and then 0.23 g of potassium tert-butoxide. (An exotherm occurred during this addition). The reaction was allowed to stir at room temperature overnight and then was heated briefly to reflux and allowed to cool. The reaction mixture was diluted with ethyl acetate and washed successively with water and then with saturated aqueous NaCl. The organic phase was dried (MgSO4), filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography (50-60% ethyl acetate/hexanes) to afford 0.48 g of the title compound of Step E (about 95% pure), a compound of the invention. 1H NMR (CDCl3): δ 7.58 (m,1H), 7.37 (m,2H), 7.23 (m,3H), 6.60 (d,2H), 4.23 (s,2H), 3.86 (s,3H), 3.41 (s,3H).

後処理

  1. addition(An exotherm occurred during this addition)
  2. temperaturewas heated briefly
  3. temperatureto reflux
  4. temperatureto cool
  5. washwashed successively with water
  6. dry with materialThe organic phase was dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by flash chromatography (50-60% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-1dcc23cfbead4e749c25dc3754f588e5
出典データセット
uspto-grants-2000_05
特許番号
US06057352

反応ノート

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